Silver is well known as an aficionado of architect Frank Lloyd Wright. In 1984, he bought the Wright-designed Storer House in Hollywood and made considerable investments to restore it to the original condition. The Storer House's squarish relief ornament then became the company logo of Silver Pictures. Silver sold it in 2002 for $2.9 million. In 1986, he purchased the long-neglected C. Leigh Stevens Auldbrass Plantation in Yemassee, South Carolina, and has been restoring it since then. Both restorations have been managed and supervised by the architect Eric Lloyd Wright, Frank Lloyd Wright's grandson. Mr. Silver also owns the 1941 Lincoln Continental once customized to Frank Lloyd Wright's design.[4]

In August 19, 2015, Silver's 28-year-old assistant Carmel Musgrove drowned in a lagoon while attending a celebration with Silver in Bora Bora, in the occasion of the marriage between Jennifer Aniston and Justin Theroux. Later, in August 2017, Musgrove's family sued Silver and his assistant Martin Herold, arguing the latter had provided her with cocaine, which contributed to her death, together with alcohol consumption and exhaustion from work.[5][6]